COUMESTROL CAS 479-13-0

Introduction：Basic information about COUMESTROL CAS 479-13-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

COUMESTROL Basic information

• Product Name: COUMESTROL
• Synonyms: cumoesterol;COUMOESTROL;7 12-DIHYDROXYCOUMESTAN 98%;Coumesterol;COUMESTROL(P);Coumestrol, >98%;3,9-dihydroxy-6-benzofuro[3,2-c][1]benzopyranone;2-(2 4-DIHYDROXYPHENYL)-6-HYDROXY-3-BENZOFURANCARBOXYLIC ACID D-LACTONE 98%
• CAS: 479-13-0
• MF: C15H8O5
• MW: 268.22
• EINECS: 207-525-6
• Product Categories: Steroids & Hormones - 13C & 2H;Steroids;Coumarins;Iso-Flavones
• Mol File: 479-13-0.mol

COUMESTROL Chemical Properties

• Melting point: ≥350 °C(lit.)
• Boiling point: 331.39°C (rough estimate)
• density: 1.2586 (rough estimate)
• refractive index: 1.7680 (estimate)
• storage temp.: Refrigerator
• solubility: DMSO: soluble
• form: Light beige solid.
• pka: 8.25±0.20(Predicted)
• color: Pale Yellow to Dark Brown
• BRN: 266702
• InChI: InChI=1S/C15H8O5/c16-7-1-3-9-11(5-7)19-14-10-4-2-8(17)6-12(10)20-15(18)13(9)14/h1-6,16-17H
• InChIKey: ZZIALNLLNHEQPJ-UHFFFAOYSA-N
• SMILES: C1(=O)OC2=CC(O)=CC=C2C2OC3=CC(O)=CC=C3C1=2
• LogP: 2.940 (est)
• CAS DataBase Reference: 479-13-0(CAS DataBase Reference)
• EPA Substance Registry System: Coumestrol (479-13-0)

Safety Information

• Hazard Codes: Xn
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: DF8077000
• F: 10
• TSCA: TSCA listed
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

COUMESTROL Usage And Synthesis

Description

Coumestrol is a phytoestrogen that occurs naturally in soybeans, spinach, and clover. It competitively (vs. 17β-estradiol, ) binds the estrogen receptors ERα (IC₅₀ = 11 nM) and ERβ (IC₅₀ = 2 nM) and can induce ER-dependent gene expression in isolated cells. Coumestrol is also a weak antagonist of pregnane X receptor (IC₅₀ = 12 μM) as well as a potential inverse agonist of the constitutive androstane receptor (EC₅₀ = 30 μM).

Chemical Properties

Yellow to Beige Powder

Uses

This compound has estrogenic activity. It exhibits bright blue fluorescence in neutral or acid solution, and greenish-yellow fluorescence in strong alkali solution.

Definition

ChEBI: A member of the class of coumestans that is coumestan with hydroxy substituents at positions 3 and 9.

Synthesis Reference(s)

Tetrahedron Letters, 4, p. 1151, 1963 DOI: 10.1039/jr9630005127

Biochem/physiol Actions

Coumestrol has anti-estrogenic actions in the brain and pituitary, mediated through estrogen receptor-α.

Safety Profile

An experimental teratogen. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

references

[1]. chen hy, dykstra kd, birzin et, et al. estrogen receptor ligands. part 1: the discovery of flavanoids with subtype selectivity. bioorg med chem lett. 2004 mar 22;14(6):1417-21.
[2]. hopert ac, beyer a, frank k, et al. characterization of estrogenicity of phytoestrogens in an endometrial-derived experimental model. environ health perspect. 1998 sep;106(9):581-6.
[3]. wang h, li h, moore lb, et al. the phytoestrogen coumestrol is a naturally occurring antagonist of the human pregnane x receptor. mol endocrinol. 2008 apr;22(4):838-57.